Dimethyl Sulfoxide → HCID 10582514, compound

Participants

Reaction Steps

To a solution of dimethyl sulfoxide (3.5 mL, 49.3 mmol) in dichloromethane (150 mL) was added dropwise oxalyl chloride (4.3 mL, 49.3 mmol) at -78° C. and the mixture was stirred for 20 rain at the same temperature. To the mixture was added dropwise a solution of 6-chloro-4-(3-hydroxypropyl)indole-2-carboxylic acid methyl ester (11.0 g, 41.1 mmol) in dichloromethane (1350 mL) at -78° C. over a period of 2 h. The mixture was stirred for 1 h at -78° C. and triethylamine (17.2 mL, 123.3 mmol) was added slowly at the same temperature. The mixture was allowed to warm at room temperature, diluted with water, and the organic layer was separated. The layer was washed with water, dried over MgSO4, and concentrated to give 12.24 g of the title compound (quant): 1H NMR (CDCl3) δ9.86 (t, 1H, J=1.0 Hz), 9.06 (bs, 1H), 7.29 (d, 1H, J=1.3 Hz), 7.22 (d, 1H, J=1.7 Hz), 6.96 (d, 1H, J=1.7 Hz), 3.96 (s, 3H), 3.20 (t, 2H, J=7.4 Hz), 2.90 (t, 2H, J=7.4 Hz).

Provenance & Evidence